US9447216B2 - Comb polymers which can be used in cosmetics and detergents - Google Patents

Comb polymers which can be used in cosmetics and detergents Download PDF

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US9447216B2
US9447216B2 US14/368,664 US201314368664A US9447216B2 US 9447216 B2 US9447216 B2 US 9447216B2 US 201314368664 A US201314368664 A US 201314368664A US 9447216 B2 US9447216 B2 US 9447216B2
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copolymer
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ethylene glycol
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Frédéric Blondel
Antonin SANNA
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SPCM SA
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
    • C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/56—Acrylamide; Methacrylamide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
    • C08F226/04—Diallylamine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/282—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
    • C08F2220/282—
    • C08F2220/285—

Definitions

  • a “comb” polymer has a structure similar to that of a comb.
  • it comprises a principal chain to which side chains are attached which may be different in nature and of variable length.
  • these side chains may have hydrophilic and/or hydrophobic properties. They may in particular be of the ethylene oxide, propylene oxide and alkyl type, and the like, with lengths of 2 to 500 units and preferably 5 to 200 units in the case of a pendant chain of the polyethylene oxide type.
  • the document EP372546 describes copolymers based on PEGMA, monomers of the C 1 -C 8 alkyl(meth)acrylamide type, and optionally cationic monomers.
  • the document JP2002-322219 describes polymers containing PEGMA units in association with hydrophobic monomers based on polypropylene glycol (PPO) or poly(tetramethylene oxide), and cationic monomers.
  • the document JP07-285831 describes hair compositions containing a polymer based on PEGMA-type monomers combined with ionic, cationic or amphoteric monomers, and additional monomers of the C 1 -C 24 alkyl(meth)acrylate type, which are mainly hydrophobic.
  • EP1769011 and EP1765893 describe polymers mainly consisting of cationic units and PEGMA units.
  • the document WO2006/013268 describes polymers comprising at least one monomer of the PEG (meth)acrylate type combined with a monomer having a cationic (cationic, amphoteric or cationic and anionic) character.
  • the document AU 2004 200 189 describes a polymer which may comprise a monomer of the PEG acrylate type combined with a monomer which may be cationic but which does not comprise a quaternary ammonium functional group.
  • the document FR 2 962 034 describes a polymer containing a monomer of the PEG methacrylate type combined with a monomer not comprising a quaternary ammonium functional group.
  • comb polymers are in particular cosmetics and detergents. They may therefore be present as a conditioner in compositions of body and hair products, or as an agent for promoting deposition in laundry detergents.
  • the applicant has developed polymers which make it possible in particular to overcome the drawbacks associated with incompatibilities between anionic species and cationic polymers.
  • the present invention thus relates to polymers which, once incorporated into a cosmetic or detergent composition, make it possible to prevent the formation of precipitates resulting from the ionic attraction between two compounds of opposite charge.
  • n is between 7 and 45.
  • the cationicity of the copolymer is advantageously between 0.3 and 2.6 meq/g, preferably between 0.5 and 1.5 meq/g.
  • water-soluble denotes a copolymer which may be dissolved in an aqueous solution, in an amount of at least 50 g/L at 25° C., without leaving insoluble particles.
  • the copolymer comprises a cationic monomer A, and a noncationic monomer B
  • cationicity(meq/g) (100 ⁇ % A )/(% A ⁇ Mw A +% B ⁇ Mw B ) in which:
  • the cationic charge density therefore depends on the proportions of monomers and their respective molar masses. Consequently, at equivalent monomer ratio, two polymers do not necessarily have the same cationic charge density considering the molar mass of each of the monomers.
  • the copolymer consists of, as percentage by mass relative to the total mass of the copolymer:
  • the copolymer has cationic charges which come solely from quaternary ammonium functional groups.
  • the cationicity of the cationic monomer(s) contained in the copolymer is exclusively due to the presence of quaternary ammonium functional groups.
  • all of the cationic charges of the copolymer come from quaternary ammonium functional groups.
  • R 2 is either a hydrogen atom; a benzyl radical; a phenyl radical optionally substituted with at least one C 1 -C 12 alkyl; a linear or branched C 1 -C 30 alkyl radical, optionally comprising at least one cyclic group, and optionally at least one aromatic group, in particular as C 1 -C 22 , or even as C 2 -C 16 , optionally comprising 1 to 4 heteroatoms chosen from O, N and S. Mention may be made in particular of the methyl, ethyl, propyl, benzyl, ethylhexyl, lauryl, stearyl and behenyl radicals.
  • the monomers of formula (I) which are quite particularly preferred may be chosen from the group comprising poly(ethylene glycol)(meth)acrylates and methylpoly(ethylene glycol)(meth)acrylates, preferably those having a molar mass of between 80 and 8000 g/mol, in particular between 300 and 2000 g/mol.
  • the cationic monomer(s) which have a quaternary ammonium functional group and which may be used in the context of the invention may be chosen in particular from monomers of the acrylamide, acrylic, vinyl, allyl or maleic type having a quaternary ammonium functional group. Mention may be made, in particular and without limitation, of quaternized dimethylaminoethyl acrylate (ADAME), quaternized dimethylaminoethyl methacrylate (MADAME), dimethyldiallylammonium chloride (DADMAC), acrylamidopropyltrimethylammonium chloride (APTAC) and methacrylamidopropyltrimethylammonium chloride (MAPTAC).
  • ADAME quaternized dimethylaminoethyl acrylate
  • MADAME quaternized dimethylaminoethyl methacrylate
  • DADMAC dimethyldiallylammonium chloride
  • ATAC acrylamidopropyl
  • the copolymer which is the subject of the present invention also comprises at least one nonionic monomer distinct from that corresponding to formula (I) above.
  • this additional nonionic monomer represents less than 25% by mass of the copolymer, advantageously from 5 to 25%.
  • the copolymer which is the subject of the invention may consist of, as percentage by mass relative to the total mass of the copolymer:
  • the nonionic monomer(s) which may be used in the context of the invention may be chosen in particular from the group comprising water-soluble vinyl monomers.
  • Preferred monomers belonging to this class are, for example, acrylamide, methacrylamide, N-isopropylacrylamide, N,N-dimethylacrylamide and N-methylolacrylamide.
  • use may be made of N-vinylformamide, N-vinylacetamide, N-vinylpyridine and N-vinylpyrrolidone, acryloylmorpholine (ACMO) and diacetone acrylamide.
  • a preferred nonionic monomer is acrylamide.
  • the water-soluble copolymer(s) may also comprise one or more hydrophobic monomers chosen in particular from monomers of the acrylamide, acrylic, vinyl, allyl or maleic type having a pendant hydrophobic functional group preferably chosen from acrylamide derivatives such as N-alkylacrylamides, for example, diacetone acrylamide, N-tert-butylacrylamide, octylacrylamide, and N,N-dialkylacrylamides such as N,N-dihexylacrylamide and acrylic acid derivatives such as alkyl acrylates and methacrylates.
  • acrylamide derivatives such as N-alkylacrylamides, for example, diacetone acrylamide, N-tert-butylacrylamide, octylacrylamide, and N,N-dialkylacrylamides such as N,N-dihexylacrylamide and acrylic acid derivatives such as alkyl acrylates and methacrylates.
  • vinyl monomers such as N-vinylformamide
  • the polymers of the invention do not require the development of a specific polymerization process. Indeed, they may be obtained according to all the polymerization techniques well known to a person skilled in the art. These may be in particular solution polymerization; gel polymerization; precipitation polymerization; (aqueous or inverse) emulsion polymerization; suspension polymerization; or micellar polymerization.
  • the polymer may be provided in liquid or solid form when its preparation includes a drying step such as spray-drying, drying on a drum or alternatively microwave drying.
  • the polymer developed by the applicant exhibits improved compatibility with anionic species.
  • anionic species is understood to mean all the macromolecular elements having an anionic character which are commonly present in cosmetic or detergent type formulations and the like.
  • the present invention also relates to the use of the copolymer described above in a cosmetic or detergent formulation.
  • these ionic species may be:
  • Anionic surfactants among which there may be mentioned, alone or mixed, salts (in particular alkali metal salts, in particular sodium salts, ammonium salts, amino salts, salts of amino alcohols or magnesium salts) of the following compounds: alkyl sulfates, alkyl ether sulfates, alkyl amido ether sulfates, alkyl aryl polyether sulfates, monoglyceride sulfates, alkyl sulfonates, alkyl phosphates, alkyl amide sulfonates, alkyl aryl sulfonates, alpha-olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkyl amide sulfosuccinates, alkyl sulfosuccinamates; alkyl sulfoacetate
  • the salts of fatty acids such as the salts of oleic, ricinoleic, palmitic and stearic
  • Anionic polyelectrolytes comprising at least one monomer having an acrylic, vinyl, maleic, fumaric or allyl functionality and containing a carboxy, phosphonate or sulfonate group, or another group having an anionic charge.
  • silicone-based polyelectrolytes comprising one or more carboxylate, sulfate, sulfonate, phosphate or phosphonate groups, or derivatives thereof.
  • Natural polymers having an anionic character which may be chosen from the group comprising polysaccharides such as cellulose, starch, guar gum, guar gum hemicellulose, gum arabic, glucomannan, carob gum, pullulan, curdlan, xanthan gum, gellan gum, carrageenan gum, dextran gum, tragacanth gum, welan gum, rhamsan gum, hyaluronic acid, inulin, pectin, lignin, chitin, alginate, agar agar or derivatives thereof.
  • polysaccharides such as cellulose, starch, guar gum, guar gum hemicellulose, gum arabic, glucomannan, carob gum, pullulan, curdlan, xanthan gum, gellan gum, carrageenan gum, dextran gum, tragacanth gum, welan gum, rhamsan gum, hyaluronic acid, inulin, pectin,
  • Polymer A comprises 75 mol % of DADMAC monomer and 25 mol % of polyethylene glycol methacrylate, i.e. 20% by mass of DADMAC and 80% by mass of polyethylene glycol methacrylate.
  • PEG 2000 MA Polyglykol® MA 2000, Clariant. It is a polyethylene glycol methacrylate whose molar mass is 2000 g/mol.
  • EDTA ethylenediaminetetraacetic acid
  • an initiator solution is prepared by introducing 0.35 g of 2,2′-azobis(2-amidinopropane)dihydrochloride (V50, Wako) in 30 g of water.
  • the temperature of the medium has reached 80° C.
  • gradual addition of the initiator solution is started.
  • the solution is added for 180 minutes and then the medium is kept at 80° C. for 120 additional minutes in order to complete the polymerization.
  • the mixture is allowed to return to room temperature and then the pH is adjusted to between 5 and 7 using an aqueous NaOH or citric acid solution at 50% by mass.
  • the product obtained is a liquid solution whose polymer concentration is 40% by mass relative to the mass of the solution.
  • the solution has a viscosity of 300 cps (Brookfield LVT, spindle 3, 30 rpm).
  • Polymer A has a comb structure. Its cationic charge density is 1.15 meq/g.
  • Polymer B comprises 98 mol % of DADMAC monomer and 2 mol % of polyethylene glycol methacrylate, i.e. 80% by mass of DADMAC and 20% by mass of polyethylene glycol methacrylate.
  • the product obtained is a liquid having a polymer concentration of 40% by mass relative to the mass of the product, and a viscosity of 1700 cps (Brookfield LVT, spindle 3, 30 rpm).
  • the polymer has a comb structure. Its cationic charge density is 4.26 meq/g.
  • the product obtained is a liquid solution whose polymer concentration is 40% by mass relative to the mass of the solution.
  • the solution has a viscosity of 200 cps (Brookfield LVT, spindle 3, 30 rpm).
  • Polymer B has a comb structure. Its cationic charge density is 6.1 meq/g.
  • the maximum mass of cationic product that can be added before the appearance of a precipitate or of a cloudiness reflecting precipitation is determined.
  • the quantity of cationic polymer introduced is then linked to a cationic charge introduced into the system.
  • the solutions containing polymer A according to the invention have a translucent appearance, whereas the solutions comprising polymers B and C contain insoluble polymer particles.
  • Polyquaternium 7 has a charge density which is included in the range claimed. However, after 2 g of polymer have been added to the solution, insoluble particles appear.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
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  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
US14/368,664 2012-01-16 2013-01-14 Comb polymers which can be used in cosmetics and detergents Active 2033-03-14 US9447216B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR1250380A FR2985727B1 (fr) 2012-01-16 2012-01-16 Nouveaux polymeres peignes utilisables en cosmetique et detergence
FR1250380 2012-01-16
PCT/FR2013/050087 WO2013107976A1 (fr) 2012-01-16 2013-01-14 Nouveaux polymeres peignes utilisables en cosmetique et detergence

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US20140378639A1 US20140378639A1 (en) 2014-12-25
US9447216B2 true US9447216B2 (en) 2016-09-20

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EP (1) EP2804880B1 (es)
CN (1) CN104039849B (es)
ES (1) ES2584386T3 (es)
FR (1) FR2985727B1 (es)
MX (1) MX2014007802A (es)
WO (1) WO2013107976A1 (es)

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FR3001457B1 (fr) * 2013-01-31 2015-02-06 Snf Sas Nouveaux polymeres peignes utilisables en cosmetique et detergence
WO2016014733A1 (en) 2014-07-23 2016-01-28 The Procter & Gamble Company Fabric and home care treatment compositions
EP3172307A1 (en) 2014-07-23 2017-05-31 The Procter and Gamble Company Treatment compositions
WO2016014802A1 (en) 2014-07-23 2016-01-28 The Procter & Gamble Company Fabric and home care treatment compositions
EP3172303B1 (en) 2014-07-23 2019-01-02 The Procter and Gamble Company Fabric and home care treatment compositions
JP6542351B2 (ja) 2014-07-23 2019-07-10 ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ 布地ケア及びホームケア処理組成物
US10519402B2 (en) 2014-07-23 2019-12-31 The Procter & Gamble Company Treatment compositions
EP3172300B1 (en) 2014-07-23 2018-12-26 The Procter and Gamble Company Fabric and home care treatment composition
CA2967001A1 (en) 2014-11-06 2016-05-12 The Procter & Gamble Company Patterned apertured webs, laminates, and methods for making the same
EP3078720A1 (fr) 2015-04-10 2016-10-12 Snf Sas Procede de deviation d'une formation souterraine
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US11261402B2 (en) 2016-01-25 2022-03-01 The Procter & Gamble Company Treatment compositions
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MX2014007802A (es) 2015-03-05
WO2013107976A1 (fr) 2013-07-25
EP2804880B1 (fr) 2016-07-06
CN104039849A (zh) 2014-09-10
US20140378639A1 (en) 2014-12-25
CN104039849B (zh) 2017-03-22
FR2985727B1 (fr) 2014-05-09
FR2985727A1 (fr) 2013-07-19
ES2584386T3 (es) 2016-09-27

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